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Rutin is a naturally active compound with biological and medical value. The traditional extraction and separation method not only destroys the structure and activity of rutin, but results in a low extraction rate. In this work, the magnetic micellar molecularly imprinted polymer of rutin with a selective recognition function, i.e., RMMMIP was synthesized from 4 to Vinylphenylboron acid and 4-Vinylpyridine as functional monomer, derivatives of cholic acid as amphiphilic molecules. The internal hydrophobic and external hydrophilic characteristics of micelle was used to weaken the solvation of rutin and strengthen the non-covalent interaction between functional monomer and rutin. Fe 3 O 4 , as the core, endowed the composite materials with good magnetic responsiveness and was easy to separate solid from liquid. Then its structure and adsorption were studied, adsorbing capacity and recognition specific factor of RMMMIP are 11.9 mg·g -1 and 3.55 respectively. RMMMIP was used for the separation of rutin from crude extracts of Sophora japonica Linn and showed a better selective adsorption capacity than quercetin, naringin and cyanidin-3-O-glucose. It indicated that RMMMIP as a specific adsorbent had the potential to be a practical way to purify rutin from rutin crude extracts in the future., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2022 Elsevier B.V. All rights reserved.)

An HPLC-UV method with high sensitivity and good resolution, calculated by the principal component external standard method with correction factors and detailed methodological validation according to ICH guidelines, was developed for the accurate detection of impurities in three different extraction processes of rutin raw materials and their tablets, and the determination of impurity profiles by LC-MS/MS. In this study, nine impurities (>0.1%) were mainly isolated and identified, four of which were process impurities, and the other five were degradation products. The results of the correlation between impurity profiles and production processes showed that the impurity content of rutin tablets correlated positively with the impurity level of the raw materials used, which correlated significantly with the extraction process. The finished rutin under the alkali-dissolution and acid-sedimentation refining method had low purity and the highest impurity content. In contrast, the number of impurities and the total amount of impurities detected in rutin by the secondary recrystallization process with methanol washing were the lowest, and were mainly process impurities. This further indicates that generating degradation impurities could be avoided, and a suitable refining process could effectively reduce impurities. This study provides an essential basis for manufacturers to optimize the process parameters of rutin raw materials. [ABSTRACT FROM AUTHOR]

The dried flower and flower bud of Styphnolobium japonicum (L.) Schott (Japanese Sophora flower and Japanese Sophora flower bud, respectively) have long been used as herbal medicines in Asia. Today, they are marketed as dietary supplements in the United States for their anti‐oxidative properties and as a source of flavonoids, including rutin and quercetin. This review focused on the safety of S. japonicum flower and flower bud as dietary supplement ingredients. No serious adverse events or toxicity were reported in the clinical or experimental animal studies we reviewed. Although some studies indicated that rutin or quercetin may have potential for drug interactions, none were identified for S. japonicum flower or flower bud. S. japonicum flower and flower bud are not known to have been associated with serious health risks when appropriately consumed in dietary supplements and have been admitted to the U.S. Pharmacopeial Convention monograph development process. However, pregnant and breastfeeding women should seek the advice of a healthcare professional because no data are available on their use by these special populations. [ABSTRACT FROM AUTHOR]

Rutin (R), a representative flavonoid found in various biomasses, can be used to prepare different fluorescent sensors for environmental, biological and medical fields. In this work, the natural R in Sophora japonica was extracted and purified to prepare fluorescent-responding sensor systems intended to recognize copper ions with both strong selectivity as well as appropriate sensitivity. Results showed that neat R had no obvious fluorescent emission peak in PBS buffer solution. However, when R and (2-hydroxypropyl)-β-cyclodextrin (CD) were introduced within buffer solution, fluorescent emission intensity was significantly increased due to the resultant R-CD inclusion complex. In addition, the formed R-CD inclusion complex was shown to behave as the aforementioned fluorescent sensor for copper ions through a mechanism of quenched fluorescent emission intensity when R-CD became bound with copper ions. The binding constant value for R-CD with copper ions was 1.33 × 106, allowing for quantification of copper ions between the concentration range of 1.0 × 10–7–4.2 × 10–6mol⋅L–1. Furthermore, the minimum detection limit was found to be 3.5 × 10–8mol⋅L–1. This work showed the prepared R-CD inclusion complex was both highly selective and strongly sensitive toward copper ions, indicating that this system could be applied into various fields where copper ions are of concern.

Extraction procedures for plant‐based secondary metabolites are mainly influenced by choice of solvent, particle size and solvent to feed ratio. For developing an extraction protocol design‐of‐experiments or model‐based approaches have widely been used. Botanical aspects such as the influence of side compounds are less investigated. Either for analytical or preparative purposes, knowledge of the underlying extraction mechanisms is required to improve the process development. In this work, we demonstrate the mechanism of accessibility limitation of rutin by side compounds depending on the solvent to feed ratio. Extraction yields of target and side compounds are analyzed to derive correlations. The role of side compounds as limiting factors for target compound accessibility is demonstrated by performing two extraction steps using three different plant species. The maximum extraction yield of rutin is reached using a solvent to feed ratio of at least 300 for all three investigated plant species, while side compounds in liquid state generally affect the extractability of rutin. Phosphatidylcholines are identified as possible accessibility‐limiting compounds. In conclusion, the yields of target and side compounds strongly depend on the solvent to feed ratio, while side compounds cover the target compound in dry matter, reducing its accessibility. [ABSTRACT FROM AUTHOR]

• One-pot system avoids complicated processing between extraction and hydrolysis. • Natural deep eutectic solvents as extractant is "greener" than organic solvents. • Enzyme catalytic is less pollution with higher yield compared to acid catalytic. • Non-aqueous system improves catalytic efficiency of rutin degrading enzyme. • This method can be used to prepare many other natural active substances. In this study, we have established a green and efficient preparation method of quercetin. Rutin was first extracted from Sophora japonica using natural deep eutectic solvents (NADESs), then hydrolyzed into quercetin by rutin degrading enzyme (RDE) obtained from germinated tartary buckwheat in situ. Rutin solubility tests showed that most of the 11 NADESs increased the solubility of rutin by 67-3116 times compared to water. Thus, NADESs could be prior candidate to extract rutin. Extraction efficiency of rutin varied with different NADESs, and a maximum of 291.57 mg g−1 was achieved in NADES ChGly, which was prepared by mixing choline chloride and glycerol at a molar ratio of 1:1. After that hydrolysis was performed directly in extraction system by adding RDE with degradation rate of up to 8.36 mg min-1·L-1. Our findings suggest that preparation of quercetin using NADESs was simple and feasible to operate, environmentally friendly, efficient, and inspired the preparation method of bioactive components from a new perspective. [ABSTRACT FROM AUTHOR]

The possibility of production of a natural antioxidant, quercetin, from flower buds of the Sophora japonica (Sophora japonica L.) using subcritical water both as a reagent and a solvent was investigated. The proposed approach allows one to avoid the use of costly and toxic organic solvents, does not require conducting separate steps of extraction and hydrolysis, and simplifies purification of the product. High quercetin yields were achieved within a time that was 13 times less than using traditional techniques. The losses of the target product during production of dry extract were reduced. [ABSTRACT FROM AUTHOR]

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The aim of this study was to find the best conditions for the extraction of rutin and quercetin from Sophora flower in acacia honey as an extractant, and to formulate a new product – honey with added value. For determination of the optimal extraction conditions of the above mentioned compounds, 10% m/m of the dried Sophora flower was added to honey and the concentration of rutin and quercetin was monitored, at 4 °C and room temperature at 1, 15, 40 and 90 day intervals. The analyses of rutin and quercetin content in honey were performed by high-performance liquid chromatography (HPLC) with ultraviolet (UV) detection. The content of rutin and quercetin in the flower was also determined to check the quality of the herbal drug used, as well as to evaluate the effectiveness of the extraction. The extraction of rutin and quercetin, in a honey sample using 10% of the Sophora flower, stored at room temperature, for 40 days, was the most intense one (150.24 mg/kg of rutin and 1338.93 mg/kg of quercetin). Sophora flower corresponds to the pharmacopoeia requirements for the quality of an herbal drug. The concentrations of rutin and quercetin in acacia honey were 0.08 and 0.14 mg/kg, respectively. The concentration of rutin in honey from the melliferous pasture of the Sophora flower was 0.40 mg/kg, while quercetin was below the detection limit (0.1 mg/kg). Honey, enriched with rutin and quercetin from Sophora flower, had sensory acceptability and pleasant taste and aroma. [Display omitted] • Honey enriched with Sophora flower is a mixture of two exceptional gifts of nature. • The best way for extraction of rutin and quercetin from honey with Sophora flowers. • Sample with 10% of the flower, stored at room t, for 40 days, was the most intense. • Honey enriched with rutin and quercetin had and pleasant taste and aroma. [ABSTRACT FROM AUTHOR]

Quantitative changes in the accumulation of the flavonol glycosides rutin and kaempferol 3-rutinoside and the isoflavone glycosides genistin and sophorabioside have been investigated in flowers and fruits of cultivated in Bulgaria Sophora japonica during ontogenetic and seasonal development. A method for extraction of flavonoids with good recovery was developed (98% for rutin and 97% for kaempferol 3-rutinoside). The subsequent high-performance liquid chromatography separation of flavonoid glycosides was achieved using Hypersil ODS C18 column and UV detection. The mobile phase comprised methanol and phosphate buffer, pH 3.23, and linear gradient elution mode within 25 min was applied. Accumulation of rutin started with initiation of the flower buds, having the maximal content up to 287 mg/g (dry weight) in mid-July during the earliest stages of flower development and tended to have high levels until mid-August. A further decrease in the amount of rutin up to 44 mg/g was found proportionally with the decline of flavonoids throughout and after the flowering period. Rutin was the predominant glycoside and can account for up to 90% of flavonoid glycoside mixture in young buds, whereas sophorabioside (64.7 mg/g, calculated as rutin equivalent) and kaempferol 3-rutinoside (46.8 mg/g) dominated at later development stages of the fruits. No significant differences in flavonoid quantity between the analysis periods of two successive years were observed. This indicated clearly the ontogenetic dependence of flavonoid formation. [ABSTRACT FROM AUTHOR]

Sophora Japonica L. (SJ) is a traditional Chinese herb used to cool blood, stop bleeding and to treat hemorrhoids with bleeding. Although several recent studies found that both SJ and Ginkgo biloba have the same components of quercetin and rutin, only Ginkgo biloba has been widely used to treat cerebrovascular disorders and dementia in humans. This study investigated the effect of SJ on cerebral infarct in rats. A total of 66 Sprague-Dawley (SD) rats were studied. Focal cerebral infarct was established by occluding the bilateral common carotid arteries and the right middle cerebral artery for 90 minutes. After 24 hours of reperfusion, the neurological status was evaluated. The rats were then killed, and brain tissue was stained with 2,3,5-triphenyl-tetrazolium chloride. The grading scale of neurological deficit and the ratio of cerebral infarction area were used as an index to evaluate the effect of SJ on cerebral infarct. In addition, the number of ED1 and interleukin-1β immunostaining positive cells, and apoptotic cells were measured in the cerebral infarction zone. The results indicated that pre-treatment with 100 or 200 mg/kg SJ and post-treatment with 200 mg/kg SJ significantly reduced the grade of neurological deficit and the ratio of cerebral infarction area. In addition, pre-treatment with 200 mg/kg SJ also significantly reduced ED1 and interleukin-1β immunostaining positive cells, and apoptotic cells in ischemia-reperfusion cerebral infarct rats. This study demonstrated that SJ could reduce the cerebral infarction area and neurological deficit induced by ischemia-reperfusion in rats, suggesting its potential as a treatment for cerebral infarct in humans. This effect of SJ involves its suppressive action of microglia, interleukin-1β and apoptosis. [ABSTRACT FROM AUTHOR]

• Dried flower buds from Sophora japonica (DFBs) comprise transglycosylating rutinosidase. • The DFBs catalyze transrutinosylation of tyrosol from rutin. • Rutinosylation of tyrosol proceeds exclusively on the primary hydroxyl. Dried flower buds of Japanese sophora (Sophora japonica) comprising rutinosidase activity were tested in rutinosylation of tyrosol via transglycosylation process from rutin. Optimal conditions for transrutinosylation of tyrosol were 49 mM rutin and 290 mM tyrosol, giving maximum conversion up to 66.4% and 24% yield of isolated and purified rutinoside. The rutinosylation proceeded exclusively on the primary hydroxyl of tyrosol, thus forming rhamnosylated derivative of salidroside. This strict regioselectivity differentiates the sophora biocatalyst from microbial rutinosidases. [ABSTRACT FROM AUTHOR]